How to Plan Long Term (Slow) Travel


Planning long term slow travel for months can be challenging, especially if you’ve never done it before.  There are several key things you can do to make it easier.  Once you have figured out your budget for the digital nomad lifestyle it’s time to start planning the journey.

Disclaimer: This article is provided for general information purposes only and is not intended to constitute professional advice. Deskless Nomad makes no representations, warranties, or guarantees, whether express or implied, that the content in the publication is accurate, complete, or up to date. Please see the full Deskless Nomad Disclaimer

Start with your bucket list

Start by creating your hit list of locations for the next year.  Think about the things you want to do at each destination including sports activities, food, cultural sites, and experiences, connecting with other digital nomads, being near friends or family, learning a language, business or volunteer opportunities, weather, or beach lifestyle.  

Consider varying your types of destinations.  You may not always want to be in a big city and you can often find better deals on accommodation outside of major cities.  Instead, you might look for medium-sized cities with lots of amenities and activities.  You may also enjoy occasionally staying in a rural location, whether it is at a jungle hostel in Peru, a farm in Tuscany, or a mountain cabin in the Andes.  Get creative!

Once you have made your list, think about the best times of year for each location based on what you plan to do there.  Don’t forget to take into account the weather, local tourist seasons, local festivals, conferences you want to attend, holidays, etc. 

Use online resources like nomadlist.com and numbeo.com to help you brainstorm ideas and research the cost of living for each location.

Choose the length of time to spend in each country

Decide how long you would like to spend in each location.  You can keep this flexible by using a range (like 1-3 months).  It is generally cheaper to stay in one place for longer due to the cost of travel when changing locations.  

The more you transition between locations, the more you will spend on transportation.  It may make more economic sense to spend an extended period of time exploring countries of a single continent or region rather than bouncing around different continents.  Flights between countries within a region will generally be cheaper and you can also take advantage of trains, buses, and ferries.  You may also be able to reduce your carbon footprint by taking public transportation rather than always flying.

Remember to check the details for each tourist visa so you don’t overstay the time limit.  Penalties can include fines, being banned from a country, or even jail time.  If you are a US citizen, you can quickly check on tourist visa lengths here.  You’ll also want to know the passport validity requirements.  Some countries will require that your passport is valid for 3-6 months beyond your planned date of departure from the country.

If you want to work remotely and stay longer in one country, consider applying for a digital nomad visa. Make sure to read about the pros and cons of these programs before applying. Alternatively there are several countries with long tourist visas where you can stay for 4 months to a year.

Start your spreadsheet like this:

Plan ahead

There are several benefits to planning at least 3-6 months ahead including:

  • Adequate time to apply for visas or visa extensions
  • The chance to secure the ideal short term rental at a good price for the full length of time you want to be there before someone else claims it.  You can also book more than one place but you risk losing out on discounts for longer stays.
  • Finding available frequent flyer award flights for fewer miles 
  • Sense of security that you have a confirmed place to go next
  • Advance warning of the funds you will need to pay any remaining balance on rentals
  • Some travel and international health insurance companies want to know which countries you will be in and when
  • Some vacation rental sites give discounts for booking multiple stays at the same time

These benefits need to be balanced with the disadvantages of planning ahead including:

  • Requires more work up front
  • Less flexibility to stay longer in one place if you really like it there
  • Having to pay for multiple flights and accommodations in advance
  • Risk of losing prepayments if your travel plans change.  To avoid losing money, always check rental cancellation policies, book flexible flights when possible, and get travel insurance.

You’ll need to figure out what works best for you.  Perhaps you feel comfortable planning only 1-2 months ahead, signing up for fare alerts, and seeing what cheap fares pop up in the meantime.  You risk needing to pay fares higher than your budget.  Early on in your digital nomad journey, you may want the security of planning further ahead.

Female tourist with backpack sitting next to lake.

Search for flights and transition transportation

Use Scott’s Cheap Flights, Momondo, or Skyscanner to search for flight deals.  With Skyscanner, you can search “Everywhere” and then scroll through until you find one of the destinations from your spreadsheet.  For your second location, you can perform the same search but put in location #1 as the city of origin.  See where the next cheap flight leads you.  As you go, add the cost of these flights to your Destination Spreadsheet.

Keep in mind that some airlines won’t let you book a one-way ticket and will ask for proof of onward travel at the check-in desk.  This means you will have to have planned and booked how you will exit the country within the visa time frame limitations. Make sure you understand the pros and cons of one-way tickets.

You’ll want to compare the cost of your flights with a round the world ticket which may be easier and cheaper depending on when and where you are going.  These types of tickets do have rules and conditions that might not fit your situation so make sure to read the fine print. The major airline alliances all offer round the world ticket options.

Use Rome2Rio to search for ways to travel by buses, trains, and ferries between your destinations. Trains and ferries may be cheaper than flights.  You can also sleep on long-distance trains and save money you would spend on accommodation.  

If you plan to lease a car in some destinations, check to see if your lease will allow you to use the car in an adjacent country where you also plan to travel.  You may be able to negotiate a lower rate for a longer car lease.

If you are booking with airline awards miles, keep in mind that some popular destinations, like New Zealand and Australia, will require planning in advance for reward travel.  You may want to start by booking your award flights to these locations and then filling in the time around them.

Some transitions between destinations may require occasional nights in a hotel or hostel if you have to get back to a major city for a flight or train trip out.  Don’t forget to include these nights in your planning.

Tourist waiting with in airport with passports and tickets.

Check multiple websites before booking your accommodation

Many properties will be listed on multiple websites but priced differently on each website.  Check multiple sites before booking to make sure you are getting the best property available for the best price.  Airbnb is a good place to start your search but there are many alternatives to Airbnb.

Don’t forget to check booking sites with rewards programs.  With the number of nights you will be staying, you can quickly rack up rewards. 

As you become more experienced with the digital nomad lifestyle you may find you prefer to use classifieds, local real estate agents, or local landlords you find through posted rental signs.  

Traveling long term can get lonely, even if you are traveling with others.  You may want to occasionally stay in co-living housing with other digital nomads, do a work exchange while you stay with a local family, or stay in a hostel to make meaningful connections with other people along the way.

Renter receiving keys from property manager.

Don’t always go for the cheapest option

Remember you get what you pay for.  Whether it’s with a budget airline or a cheap rental.  Know your travelers’ rights if your flight is canceled or delayed.  Learn how to protect yourself from short terms and vacation rental scams.  

Many vacation and short-term rental sites will list weekly and monthly discounts.  If you see a place you like but the price is too high or there is no monthly discount, contact the host to negotiate a lower price for a longer stay.  Some booking websites also offer services to negotiate with the host for you.  

Don’t commit to a long stay in a place you haven’t seen in person

Make sure you know the cancellation policy in case you arrive and the place doesn’t match what you were expecting.  If you plan on a long stay, negotiate a flexible month-to-month lease in case you want to change accommodations early.

Keep a spreadsheet of your future bookings

I recommend using a spreadsheet to keep track of your bookings.  A spreadsheet will help you stick to your average budget, anticipate future payments due, quickly find particular properties you want to revisit, and assist with expenses at tax time for work-related trips.  This will make your life so much easier! Enter the following details for each property:  

  • Property address
  • Link to property listing online
  • Date of stay
  • Date booked
  • Deposit paid at time of booking
  • Remaining payment due
  • Date next payment due 
  • Additional fees due on arrival (linens, cleaning, stocked fridge, pool heating)
  • Total cost
  • Landlord contact details
  • Cancellation policy
  • Rewards earned
Example spreadsheet for future bookings

Strategize your travel hacking and book everything on credit cards that reward your purchases

Make sure you join the frequent flyer programs for the airlines you use to collect miles for all of your flights.  Some vacation rental websites also partner with airline frequent flyer programs.

Learn how to travel hack with travel credit cards, points, and other offers with ThePointsGuy.

Get health and travel insurance

Don’t forget to make sure your travel insurance covers all of your bookings.  Some travel insurance companies will only cover trips of a certain length so check the fine print. Most travel insurance will cover lost baggage, delayed flights, and cancellations under certain conditions.  You will also want to check if they cover Covid-19 quarantine in case you test positive prior to a flight out and are required to quarantine in a local hotel.

Overestimate your budget by 25%

Be prepared that things will likely cost more than you expect.  Even with careful planning, you may encounter extra fees and expensive last-minute changes.  Things don’t always go as planned on the road so make sure you overestimate how much you will spend and keep extra funds available for the unexpected.  Learn more about how to budget for the digital nomad lifestyle.

If you plan to work remotely during long-term travel, make sure you understand how taxes are handled for digital nomads and remote workers abroad.

Jamie Dubois

I am a freelance writer, wanderer, kayaker, rock climber, and adventurer exploring the world on my own terms.

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